# Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Alastair Florence' _publ_contact_author_email ALASTAIR.FLORENCE@STRATH.AC.UK _publ_section_title ; A Predicted Dimer-based Polymorph of 10,11-Dihydrocarbamazepine (Form IV) ; loop_ _publ_author_name 'Alastair Florence' 'Jean-Baptiste Arlin' 'Andrea Johnston' 'Alan R. Kennedy' 'Gary Miller' ; S.L.Price ; # Attachment 'DHC-FormIV-Final.cif' data_Dihydrocarbamazepine_form_IV_SX_structure _database_code_depnum_ccdc_archive 'CCDC 739821' _chemical_name_systematic 10,11-Dihydro-5H-dibenzo(b,f)azepine-5-carboxamide _chemical_name_common 10,11-Dihydro-5H-dibenzo(b,f)azepine-5-carboxamide _chemical_formula_sum 'C15 H14 N2 O' _chemical_formula_moiety 'C15 H14 N2 O' _chemical_formula_weight 238.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.207(6) _cell_length_b 5.347(2) _cell_length_c 18.891(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.37(2) _cell_angle_gamma 90.00 _cell_volume 1195.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1650 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 24.86 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_preparation sublimation _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; This is a polymorph of dihydrocarbamazepine, termed form IV. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16837 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2353 _reflns_number_gt 1566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.1319P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2353 _refine_ls_number_parameters 171 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.77324(15) 0.0123(3) 0.04367(10) 0.0184(4) Uani 1 1 d . . . C2 C 0.76153(15) 0.1996(3) 0.09097(10) 0.0227(4) Uani 1 1 d . . . H1 H 0.6888 0.2663 0.0783 0.027 Uiso 1 1 calc R . . C3 C 0.85463(15) 0.2892(4) 0.15608(10) 0.0248(4) Uani 1 1 d . . . H2 H 0.8458 0.4140 0.1887 0.030 Uiso 1 1 calc R . . C4 C 0.96094(16) 0.1957(3) 0.17339(11) 0.0252(4) Uani 1 1 d . . . H3 H 1.0256 0.2575 0.2176 0.030 Uiso 1 1 calc R . . C5 C 0.97231(16) 0.0121(3) 0.12597(10) 0.0229(4) Uani 1 1 d . . . H4 H 1.0457 -0.0496 0.1383 0.027 Uiso 1 1 calc R . . C6 C 0.87968(15) -0.0863(3) 0.06045(10) 0.0184(4) Uani 1 1 d . . . C7 C 0.90431(15) -0.2900(3) 0.01426(10) 0.0227(4) Uani 1 1 d . . . H5 H 0.9465 -0.4242 0.0520 0.027 Uiso 1 1 calc R . . H6 H 0.9557 -0.2185 -0.0058 0.027 Uiso 1 1 calc R . . C8 C 0.80518(15) -0.4127(3) -0.05575(10) 0.0233(4) Uani 1 1 d . . . H7 H 0.8349 -0.5404 -0.0796 0.028 Uiso 1 1 calc R . . H8 H 0.7560 -0.4986 -0.0363 0.028 Uiso 1 1 calc R . . C9 C 0.73608(14) -0.2268(3) -0.11795(10) 0.0188(4) Uani 1 1 d . . . C10 C 0.73414(15) -0.2144(4) -0.19213(10) 0.0242(4) Uani 1 1 d . . . H9 H 0.7767 -0.3310 -0.2060 0.029 Uiso 1 1 calc R . . C11 C 0.67036(15) -0.0324(4) -0.24610(11) 0.0260(5) Uani 1 1 d . . . H10 H 0.6699 -0.0253 -0.2965 0.031 Uiso 1 1 calc R . . C12 C 0.60757(16) 0.1383(4) -0.22721(11) 0.0253(5) Uani 1 1 d . . . H11 H 0.5640 0.2619 -0.2644 0.030 Uiso 1 1 calc R . . C13 C 0.60856(15) 0.1280(3) -0.15360(10) 0.0219(4) Uani 1 1 d . . . H12 H 0.5663 0.2455 -0.1398 0.026 Uiso 1 1 calc R . . C14 C 0.67148(15) -0.0547(3) -0.10034(10) 0.0177(4) Uani 1 1 d . . . C15 C 0.59446(14) -0.2233(3) -0.01579(10) 0.0191(4) Uani 1 1 d . . . N1 N 0.67287(12) -0.0699(3) -0.02364(8) 0.0180(4) Uani 1 1 d . . . N2 N 0.59931(13) -0.2466(3) 0.05591(9) 0.0221(4) Uani 1 1 d D . . O1 O 0.52238(10) -0.3361(2) -0.07474(7) 0.0260(3) Uani 1 1 d . . . H13 H 0.5515(14) -0.359(3) 0.0599(12) 0.042(6) Uiso 1 1 d D . . H14 H 0.6484(15) -0.152(4) 0.0953(9) 0.058(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0243(10) 0.0152(9) 0.0162(9) 0.0008(7) 0.0094(8) -0.0040(8) C2 0.0249(10) 0.0211(10) 0.0246(10) -0.0025(8) 0.0133(8) -0.0013(8) C3 0.0304(11) 0.0228(10) 0.0224(10) -0.0059(8) 0.0128(8) -0.0040(9) C4 0.0276(10) 0.0242(10) 0.0196(9) -0.0029(9) 0.0067(8) -0.0044(9) C5 0.0228(10) 0.0224(10) 0.0223(10) 0.0029(8) 0.0089(8) 0.0009(8) C6 0.0253(10) 0.0140(9) 0.0167(9) 0.0042(7) 0.0101(8) -0.0008(8) C7 0.0259(10) 0.0203(10) 0.0218(10) 0.0021(8) 0.0105(8) 0.0035(8) C8 0.0300(11) 0.0157(9) 0.0252(10) -0.0020(8) 0.0131(9) 0.0016(8) C9 0.0216(9) 0.0160(9) 0.0183(9) -0.0027(7) 0.0083(8) -0.0051(8) C10 0.0246(10) 0.0273(11) 0.0234(10) -0.0076(9) 0.0130(8) -0.0039(8) C11 0.0288(11) 0.0330(11) 0.0177(9) -0.0013(9) 0.0118(9) -0.0086(9) C12 0.0295(11) 0.0234(10) 0.0199(10) 0.0040(8) 0.0081(8) -0.0011(9) C13 0.0246(10) 0.0192(10) 0.0215(10) -0.0020(8) 0.0099(8) -0.0008(8) C14 0.0226(10) 0.0164(9) 0.0154(9) -0.0020(8) 0.0095(8) -0.0060(8) C15 0.0212(9) 0.0154(9) 0.0223(10) -0.0005(8) 0.0111(8) -0.0003(8) N1 0.0222(8) 0.0189(8) 0.0152(7) -0.0004(6) 0.0104(6) -0.0041(6) N2 0.0296(9) 0.0225(9) 0.0173(8) -0.0021(7) 0.0133(7) -0.0104(7) O1 0.0295(7) 0.0270(7) 0.0212(7) -0.0028(6) 0.0110(6) -0.0094(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.396(2) . ? C1 C6 1.400(3) . ? C1 N1 1.439(2) . ? C2 C3 1.382(2) . ? C2 H1 0.9500 . ? C3 C4 1.386(3) . ? C3 H2 0.9500 . ? C4 C5 1.381(3) . ? C4 H3 0.9500 . ? C5 C6 1.400(2) . ? C5 H4 0.9500 . ? C6 C7 1.518(2) . ? C7 C8 1.535(2) . ? C7 H5 0.9900 . ? C7 H6 0.9900 . ? C8 C9 1.499(2) . ? C8 H7 0.9900 . ? C8 H8 0.9900 . ? C9 C10 1.392(2) . ? C9 C14 1.392(2) . ? C10 C11 1.390(3) . ? C10 H9 0.9500 . ? C11 C12 1.383(3) . ? C11 H10 0.9500 . ? C12 C13 1.386(2) . ? C12 H11 0.9500 . ? C13 C14 1.384(2) . ? C13 H12 0.9500 . ? C14 N1 1.443(2) . ? C15 O1 1.252(2) . ? C15 N2 1.333(2) . ? C15 N1 1.380(2) . ? N2 H13 0.898(5) . ? N2 H14 0.896(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.73(16) . . ? C2 C1 N1 117.68(16) . . ? C6 C1 N1 121.57(16) . . ? C3 C2 C1 120.71(17) . . ? C3 C2 H1 119.6 . . ? C1 C2 H1 119.6 . . ? C2 C3 C4 119.49(18) . . ? C2 C3 H2 120.3 . . ? C4 C3 H2 120.3 . . ? C5 C4 C3 119.61(17) . . ? C5 C4 H3 120.2 . . ? C3 C4 H3 120.2 . . ? C4 C5 C6 122.43(18) . . ? C4 C5 H4 118.8 . . ? C6 C5 H4 118.8 . . ? C1 C6 C5 117.00(17) . . ? C1 C6 C7 126.15(15) . . ? C5 C6 C7 116.84(16) . . ? C6 C7 C8 118.91(15) . . ? C6 C7 H5 107.6 . . ? C8 C7 H5 107.6 . . ? C6 C7 H6 107.6 . . ? C8 C7 H6 107.6 . . ? H5 C7 H6 107.0 . . ? C9 C8 C7 112.41(15) . . ? C9 C8 H7 109.1 . . ? C7 C8 H7 109.1 . . ? C9 C8 H8 109.1 . . ? C7 C8 H8 109.1 . . ? H7 C8 H8 107.9 . . ? C10 C9 C14 118.04(16) . . ? C10 C9 C8 123.59(17) . . ? C14 C9 C8 118.37(16) . . ? C11 C10 C9 120.39(18) . . ? C11 C10 H9 119.8 . . ? C9 C10 H9 119.8 . . ? C12 C11 C10 120.69(18) . . ? C12 C11 H10 119.7 . . ? C10 C11 H10 119.7 . . ? C11 C12 C13 119.55(18) . . ? C11 C12 H11 120.2 . . ? C13 C12 H11 120.2 . . ? C14 C13 C12 119.52(18) . . ? C14 C13 H12 120.2 . . ? C12 C13 H12 120.2 . . ? C13 C14 C9 121.79(16) . . ? C13 C14 N1 120.37(16) . . ? C9 C14 N1 117.84(15) . . ? O1 C15 N2 122.20(16) . . ? O1 C15 N1 120.07(16) . . ? N2 C15 N1 117.73(15) . . ? C15 N1 C1 121.84(14) . . ? C15 N1 C14 117.78(14) . . ? C1 N1 C14 117.77(14) . . ? C15 N2 H13 115.4(14) . . ? C15 N2 H14 118.8(15) . . ? H13 N2 H14 126(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(3) . . . . ? N1 C1 C2 C3 -179.32(16) . . . . ? C1 C2 C3 C4 1.5(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? N1 C1 C6 C5 178.08(15) . . . . ? C2 C1 C6 C7 179.82(17) . . . . ? N1 C1 C6 C7 -1.9(3) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C4 C5 C6 C7 -179.14(17) . . . . ? C1 C6 C7 C8 -2.9(3) . . . . ? C5 C6 C7 C8 177.18(16) . . . . ? C6 C7 C8 C9 58.7(2) . . . . ? C7 C8 C9 C10 110.0(2) . . . . ? C7 C8 C9 C14 -69.0(2) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C11 -178.23(16) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C12 C13 C14 C9 1.3(3) . . . . ? C12 C13 C14 N1 -179.48(16) . . . . ? C10 C9 C14 C13 -1.4(2) . . . . ? C8 C9 C14 C13 177.75(16) . . . . ? C10 C9 C14 N1 179.39(15) . . . . ? C8 C9 C14 N1 -1.5(2) . . . . ? O1 C15 N1 C1 -164.03(16) . . . . ? N2 C15 N1 C1 15.6(2) . . . . ? O1 C15 N1 C14 -2.8(2) . . . . ? N2 C15 N1 C14 176.83(16) . . . . ? C2 C1 N1 C15 -75.4(2) . . . . ? C6 C1 N1 C15 106.2(2) . . . . ? C2 C1 N1 C14 123.30(18) . . . . ? C6 C1 N1 C14 -55.1(2) . . . . ? C13 C14 N1 C15 91.9(2) . . . . ? C9 C14 N1 C15 -88.84(19) . . . . ? C13 C14 N1 C1 -106.07(19) . . . . ? C9 C14 N1 C1 73.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.197 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.045